Mutual Opportunities
Head of Worksite Product Development
Springfield, Massachusetts; Boston, Massachusetts; New York, New York
Thank you to our employees for voting us one of the top places to work in Massachusetts for seven consecutive years!
Overview
A career with us means you’ll work alongside exceptional people and be empowered to reach your professional and personal goals. Our employees are at the foundation of what enables MassMutual to deliver on our purpose to help people secure their futures and protect the ones they love.
We embrace the idea that we all are stronger and better through our support for one another. We strive to create a culture where employees feel valued and are celebrated for who they are.
“Since our founding in 1851, mutuality has put our policyowners at the center of everything we do. At our core, we’re a company of people helping people in their time of need, and that spirit extends to the culture we’ve built at our company. Our employees support and rely on each other each day, collaborating to deliver the best solutions for our customers and help millions more secure their future and protect the ones they love.”
Job Description
The Opportunity
MassMutual is seeking a highly experienced and influential Head of Worksite Product Development to lead the strategy, design, manufacturing, and ongoing evolution of our Worksite Voluntary Benefits portfolio, including Group Whole Life and Supplemental Health. This leader will shape the enterprise Worksite strategy, drive competitive differentiation, and partner across functions to build innovative, scalable, and financially sound products that resonate with employers, employees, and distributors.
This role requires deep market expertise, strong actuarial or product development experience, and exceptional communication skills to translate product value stories into compelling narratives that strengthen distribution engagement and market positioning.
The Team
You will join a high performing, collaborative team responsible for advancing MassMutual’s strategies through disciplined product manufacturing and innovation. The team partners closely with distribution, pricing, underwriting, operations, technology, and shared services to deliver meaningful Worksite insurance solutions.
The Impact
Product Strategy & Leadership
Define and deliver the enterprise Worksite product strategy and value proposition across Voluntary Benefits.
Translate market intelligence and competitive trends into differentiated product strategies and long-term roadmaps.
Product Development & Pricing Governance
Lead full lifecycle product development, from feasibility and concept evaluation through design, implementation, and ongoing management.
Develop product specifications, contract definitions, illustrations, and scalable product architecture.
Ensure strong alignment with pricing, underwriting, risk, and actuarial governance practices.
Cross Functional Execution & Operational Readiness
Partner with project management, operations, finance, legal, IT, distribution, and other stakeholders to assess impacts and ensure a seamless product launch.
Create clear documentation—including process flows, mockups, and design examples—to support shared understanding across teams.
Market & Portfolio Insights
Anticipate and shape the future of Worksite voluntary benefits, incorporating trends such as workforce demographics, enrollment experience expectations, and personalization needs.
Analyze internal performance data to identify opportunities for improvement and innovation.
Value Storytelling & Stakeholder Influence
Develop and deliver compelling product stories that articulate value propositions and market fit for distributors, employers, and employees.
Present strategic recommendations and product insights to senior leadership and distribution partners.
Leadership & Development
Lead through influence across a highly matrixed organization, setting product standards and aligning stakeholders without direct authority. Coach, mentor, and develop talent across the Worksite product organization and matrixed teams.
Foster a collaborative, high performance culture grounded in innovation, accountability, and continuous improvement.
Qualifications
8+ years of experience in insurance product development, Worksite voluntary benefits, pricing/actuarial functions, or related fields.
Strong understanding of industry trends, competitive landscape, and Worksite distribution relationships.
Demonstrated ability to lead complex, cross functional initiatives in a highly matrixed environment.
Exceptional analytical, problem solving, and strategic thinking skills.
Outstanding communication abilities with capability to simplify complex concepts for diverse stakeholder groups.
Fellow of the Society of Actuaries (FSA) preferred.
#LI-LS1
MassMutual is an equal employment opportunity employer. We welcome all persons to apply.If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
California residents: For detailed information about your rights under the California Consumer Privacy Act (CCPA), please visit our California Consumer Privacy Act Disclosures page.
MassMutual will accept applications on an ongoing basis until such time as a candidate has been offered employment. The job description includes the main duties of this position, which may evolve over time. You may be required to perform other duties not listed.
It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment.
Salary Range: $167,800-$220,200
Hiring Process
Explore
Explore our open jobs by clicking 'search jobs' to find a position that aligns with your experience and skills. You may also consider joining our Talent Network.
Apply
Click the “apply” button on that job posting to complete and submit your application. Your application will be reviewed by a recruiter, which, due to the volume of applications received, may take some time as we carefully consider each application.
Screen
After your application has been reviewed, if you meet the qualifications for the role, a recruiter will reach out to you to start a conversation.
Interview
If you are invited for an interview, you will be scheduled to meet with the hiring manager and hiring team.
Offer
If you are extended an offer to join MassMutual and accept, your start will be contingent upon a satisfactory background check.
Hire
If you accept the offer, we will be so excited to welcome you to the MassMutual community!
If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
By the numbers*
- 85% of employee respondents say they are proud to work at MassMutual
-
90
% of employee respondents say the work they do at MassMutual is meaningful - 85% of employee respondents say they feel encouraged to come up with new and better ways of doing things
*Source: 2025 MassMutual employee engagement survey
Award-Winning Culture
MassMutual is guided by a single purpose: We help people secure their future and protect the ones they love. As a company operated for the benefit of our members and participating policyowners, we are defined by mutuality and our vision to provide financial well-being for all Americans. It’s more than our company structure — it’s our way of life. We are a company of people protecting people. Our company exists because people are willing to share risk and resources and rely on each other when it counts.
We strive to build a thriving community where everyone is valued, included, and feels that they belong.
At MassMutual, we Live Mutual.
How We Work
MassMutual’s flexible workplace approach combines the importance of connecting in person and the flexibility of working remotely. Our hybrid model puts collaboration first with employees coming in at least three days per week to our spectacular campus settings and also enjoying the flexibility of remote Fridays, company-wide remote weeks, and a bank of flexible remote weeks to use throughout the year.
Benefits for the whole you (and your loved ones)
There’s more to your life than your job and there’s more to your aspirations than a paycheck. We take a holistic view of compensation and benefits that provides the flexibility to create a healthy balance in your life for work, family, and community. We offer the benefits you’d expect, like medical, dental, 401(k), and generous vacation time, but we also offer ones you might not expect, like three paid days for volunteering, a $1,250 annual Well-Being Wallet, and up to 320 hours of caregiver leave.
Explore some of our offerings below. Benefit details can be found here.
Why MassMutual?
Candy
Marketing Consultant
Atsam
Head of Advisor/Client Experience & Business Excellence
Erica
Head of Procurement
where we work
Springfield Office
1295 State Street, Springfield, MA
Boston Office
10 Fan Pier Blvd, Boston, MA
New York Office
2 Park Ave,
New York, NY
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